Triethylamine → 2-(4-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963269노트

반응식

HRID 1963269 반응식
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15]C)=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66735290Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 667316402-(4-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid수율 80.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate (5.797 g, 18.74 mmol) was dissolved in acetonitrile (60 mL) and water (1.2 mL), then lithium bromide (13.02 g, 149.92 mmol) was added. Triethylamine (10.39 mL, 74.96 mmol) was added and the resulting yellow suspension was heated at reflux for 1.5 h. water (60 mL) and MTBE (120 mL) were added. The organic phase was extracted with water (×2). The pooled aqueous layer was acidified to pH 1 with 3.8 M HCl and then extracted with MTBE (×2). The combined organic layer was washed with water and evaporated. Traces of water were azeotropically removed by MeCN. 2-(4-Fluorobenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.43 g, 80%) was isolated as a beige solid. MS m/z 296 (M+H)+

후처리

  1. temperaturethe resulting yellow suspension was heated
  2. additionwere added
  3. extractionThe organic phase was extracted with water (×2)
  4. extractionextracted with MTBE (×2)
  5. washThe combined organic layer was washed with water
  6. customevaporated
  7. customTraces of water were azeotropically removed by MeCN

출처 및 근거

ORD 기록
ord-8e5e82ee04b34bb98348e875bf29e895
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415378B2

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